Sodium Acetate → HCID 9938116, compound

HRID 858046Notes

Reaction equation

HRID 858046 reaction equation
[CH:1]1([CH2:4][N:5]2[C:13]3[N:12]=[C:11]([CH2:14][C:15]4[CH:20]=[CH:19][C:18]([NH:21][S:22]([C:25]5[C:26]([CH3:32])=[N:27][N:28]([CH3:31])[C:29]=5Cl)(=[O:24])=[O:23])=[CH:17][CH:16]=4)[NH:10][C:9]=3[C:8](=[O:33])[N:7]([CH2:34][C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=3[F:41])[C:6]2=[O:42])[CH2:3][CH2:2]1.C([O-])(=O)C.[Na+]>C(Cl)Cl.CO.CO.C(Cl)Cl.[Pd]>[CH:1]1([CH2:4][N:5]2[C:13]3[N:12]=[C:11]([CH2:14][C:15]4[CH:20]=[CH:19][C:18]([NH:21][S:22]([C:25]5[C:26]([CH3:32])=[N:27][N:28]([CH3:31])[CH:29]=5)(=[O:23])=[O:24])=[CH:17][CH:16]=4)[NH:10][C:9]=3[C:8](=[O:33])[N:7]([CH2:34][C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=3[F:41])[C:6]2=[O:42])[CH2:3][CH2:2]1

Participants

7

Reactant 2

HCID 517045Sodium AcetateHCID 10258200HCID 10258200, compound

Product 1

HCID 9938116HCID 9938116, compoundYield 65%

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

A mixture of 5-chloro-1,3-dimethyl-1H-pyrazole-4-sulfonic acid {4-[3-cyclopropylmethyl-1-(2-fluoro-benzyl)-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-ylmethyl]-phenyl}-amide (300 mg, 0.49 mmol) in methylene chloride (125 mL) and methanol (125 mL) at 25° C. was treated with 10% Pd/C (1.0 g) and sodium acetate (134 mg, 1.22 mmol). The resulting mixture was hydrogenated in a Parr bomb at 50 psi for 24 h. At this time, the reaction was filtered through a pad of celite and was washed with an 8/2 methylene chloride/methanol solution (200 mL). The filtrate was concentrated in vacuo to afford a white solid. This solid was dissolved in a 5/95 methanol/methylene chloride solution. The organics were washed with water (1×25 mL). The aqueous layer was then back-extracted with chloroform (1×50 mL). The combined organics were dried over magnesium sulfate, filtered, and concentrated in vacuo to afford 1,3-dimethyl-1H-pyrazole-4-sulfonic acid {4-[3-cyclopropylmethyl-1-(2-fluoro-benzyl)-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-ylmethyl]-phenyl}-amide (184 mg 65%) as a white solid; (ES)+-HRMS m/e calculated for C28H28FN7O4S (M+H)+ 578.1980, found 578.1987.

Workup

  1. filtrationAt this time, the reaction was filtered through a pad of celite
  2. washwas washed with an 8/2 methylene chloride/methanol solution (200 mL)
  3. concentrationThe filtrate was concentrated in vacuo
  4. customto afford a white solid
  5. washThe organics were washed with water (1×25 mL)
  6. extractionThe aqueous layer was then back-extracted with chloroform (1×50 mL)
  7. dry with materialThe combined organics were dried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b3f206a4dd3b439581b0f8b83afe0286
Source dataset
uspto-grants-2006_12
Patent number
US07148229B2

Reaction notes

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